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Pyritinol

Chemical compound


Chemical compound

FieldValue
Verifiedfieldschanged
verifiedrevid464377508
IUPAC_name5,5'-[dithiobis(methylene)]bis[4-(hydroxymethyl)-2-methylpyridin-3-ol]
imagePyritinol.svg
image_classskin-invert-image
elimination_half-life2.5 hours
CAS_number_Ref
CAS_number1098-97-1
ATC_prefixN06
ATC_suffixBX02
PubChem14190
DrugBank_Ref
ChemSpiderID_Ref
ChemSpiderID13561
UNII_Ref
UNIIAK5Q5FZH2R
KEGG_Ref
KEGGD02160
ChEMBL_Ref
ChEMBL488093
C16H=20N=2O=4S=2
smilesOc1c(c(cnc1C)CSSCc2c(c(O)c(nc2)C)CO)CO
StdInChI_Ref
StdInChI1S/C16H20N2O4S2/c1-9-15(21)13(5-19)11(3-17-9)7-23-24-8-12-4-18-10(2)16(22)14(12)6-20/h3-4,19-22H,5-8H2,1-2H3
StdInChIKey_Ref
StdInChIKeySIXLXDIJGIWWFU-UHFFFAOYSA-N

| elimination_half-life = 2.5 hours

Pyritinol also called pyridoxine disulfide or pyrithioxine (European drug names Encephabol, Encefabol, Cerbon 6) is a semi-synthetic water-soluble analog of vitamin B6 (Pyridoxine HCl). It was produced in 1961 by Merck Laboratories by bonding 2 vitamin B6 compounds (pyridoxine) together with a disulfide bridge. Since the 1970s, it has been a prescription and OTC drug in several countries for cognitive disorders, rheumatoid arthritis, and learning disorders in children. Since the early 1990s it has been sold as a nootropic dietary supplement in the United States.

Availability

It is approved for "symptomatic treatment of chronically impaired brain function in dementia syndromes" and for "supportive treatment of sequelae of craniocerebral trauma" in various European countries, including Austria, Germany, France, Italy, Portugal, and Greece. In France it is also approved for rheumatoid arthritis as a disease modifying drug, on the basis of the results of clinical trials. In many countries it is available over the counter and is widely advertised on the internet as being for "memory disturbances."

Adverse effects

Adverse effects include nausea, headache, and rarely allergic reaction (mild skin reactions). A 2004 survey of six case reports suggested a link between pyritinol and severe cholestatic hepatitis when on several drugs for certain diseases.

Other rare side effects: acute pancreatitis and photoallergic eruption.

References

References

  1. (May 1993). "Comparison of pyritinol and auranofin in the treatment of rheumatoid arthritis. The European Multicentre Study Group". British Journal of Rheumatology.
  2. (1993). "Erythema multiforme-like eruption in association with severe headache following pyritinol". Dermatology.
  3. (1994). "Unwanted Effects of Cosmetics and Drugs Used in Dermatology". Elsevier.
  4. (March 2004). "Severe cholestatic hepatitis induced by pyritinol". BMJ.
  5. (August 1998). "Acute pancreatitis due to pyritinol: an immune-mediated phenomenon". Gastroenterology.
  6. (October 1996). "Photoallergic drug eruption due to pyridoxine hydrochloride". The Journal of Dermatology.
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